The other day, a friend of mine asked me whether CEOs were born or made. I said, “That’s kind of like asking if Jolly Ranchers are grown or made. CEO is a very unnatural job.” After saying it and seeing the surprised look on his face, I realized that perhaps it wasn’t as obvious as I’d originally thought.

After thinking further, I realized that most people actually assume the opposite—CEOs are born not made. I often listen as other Venture Capitalists and board members rapidly evaluate a founder and conclude that she’s not “CEO material”. I am not sure how they figure these things out so fast. It generally takes years for a founder to develop the CEO skill set and it is usually extremely difficult for me to tell whether or not she will make it.

In athletics, some things like becoming a sprinter can be learned relatively quickly because they take a natural motion and refine it. Others, like boxing, take much longer to master, because they require lots of unnatural motions. For example, when going backwards in boxing, it’s critically important to pick up your back foot first, because if you get hit while walking backwards the natural way—picking up your front foot first—often leads to getting knocked cold. Learning to make this unnatural motion feel natural takes a great deal of practice. If you do what feels most natural as a CEO, then you may also get knocked cold.

Being CEO requires lots of unnatural motion. From an anthropological standpoint, it is natural to do things that make people like you. It enhances your chances for survival. Yet to be a good CEO, in order to be liked in the long run, you must do many things that will upset people in the short run. Unnatural things.

In fact, even the most basic CEO building blocks will feel unnatural at first. If your buddy tells you a funny story, it would feel quite weird to evaluate her performance. It would be totally unnatural to say: “Gee, I thought that story really sucked. It had potential, but you were underwhelming on the build up then you totally flubbed the punch line. I suggest that you go back, rework it and present it to me again tomorrow.” Doing so would be quite bizarre, but evaluating people’s performances and constantly giving feedback is precisely what a CEO must do. If she doesn’t, then the more complex motions such as writing reviews, taking away territory, handling politics, setting compensation and firing people will be either impossible or handled rather poorly.

Giving feedback turns out to be the unnatural atomic building block atop which the unnatural skill set of management gets built. But how does one master the unnatural?

The Shit Sandwich

A popular and sometimes effective technique for feedback beginners is something that experienced managers call The Shit Sandwich. The technique is marvelously described in the classic management text, The One Minute Manager. The basic idea is that people open up to feedback far more if you start by complimenting them (slice of bread #1), then you give them the difficult message (the shit), then wrap up by reminding them how much you value their strengths (slice of bread #2). The shit sandwich also has the positive side effect of focusing the feedback on the behavior rather than the person, because you establish up front that you really value the person. This is a key concept in giving feedback.

The shit sandwich can work well with junior employees, but has the following challenges:

It tends to be overly formal. Because you have to preplan and script the sandwich to make it come out correctly, the process can feel formal and judgmental to the employee.

After you do it a couple of times, it will lack authenticity. The employee will think: “Oh boy, she’s complimenting me again. I know what’s coming next, the shit.”

More senior executives will recognize the shit sandwich immediately and it will have an instant negative effect.

Early in my career, I attempted to deliver a carefully crafted shit sandwich to a senior employee and she looked at me like I was a little kid and said: “Spare me the compliment, Ben, and just tell me what I did wrong.” At that point, I thought that I was definitely not born to be a CEO.

The Keys

To become elite at giving feedback, you must elevate yourself beyond a basic technique like the shit sandwich. You must develop a style that matches your own personality and values. Here are the keys to being effective:

Be authentic. It’s extremely important that you believe in the feedback that you give and not say anything to manipulate the recipient’s feelings. You can’t fake the funk.

Come from the right place. It’s important that you give people feedback because you want them to succeed and not because you want them to fail. If you really want someone to succeed, then make her feel it. Make her feel you. If she feels you and you are in her corner, then she will listen to you.

Don’t get personal. If you decide to fire somebody, fire her. Don’t prepare her to get fired. Prepare her to succeed. If she doesn’t take the feedback, then that’s a different conversation.

Don’t clown people in front of their peers. While it’s OK to give certain kinds of feedback in a group setting, you should strive never to embarrass someone in front of their peers. If you do so, then your feedback will have little impact other than to a) cause the employee to be horribly ashamed and b) cause the employee to hate your guts.

Feedback is not one size fits all. Everybody is different. Some employees are extremely sensitive to feedback while others have particularly thick skin and often thick skulls. Stylistically, your tone should match the employee’s personality not your mood.

Be direct, but not mean. Don’t be obtuse. If you think somebody’s presentation sucks, don’t say: “It’s really good, but could use one more pass to tighten up the conclusion.” While it may seem harsh, it’s much better to say: “I couldn’t follow it and I didn’t understand your point and here are the reasons why.” Watered down feedback can be worse than no feedback at all because it’s deceptive and confusing to the recipient. But don’t beat them up or attempt to show your superiority. Doing so will defeat your purpose because when done properly feedback is dialogue, not a monologue.

Feedback is a dialogue, not a monologue

You may be the CEO and you may be telling somebody about something that you don’t like or disagree with, but that doesn’t mean that you’re right. Your employee should know more about her function than you. She should have more data than you. You may be wrong.

As a result, your goal should be for your feedback to open up rather than close down discussion. Encourage people to challenge your judgment and argue the point to conclusion. Culturally, you want super high standards thoroughly discussed. You want to apply tremendous pressure to get the highest quality thinking, yet be open enough to find out when you are wrong.

High frequency feedback

Once you’ve mastered the keys, you should practice what you’ve mastered all the time. As CEO, you should have an opinion on absolutely everything. You should have an opinion on every forecast, every product plan, every presentation and even every comment. Let people know what you think. If you like someone’s comment, give her the feedback. If you disagree, give her the feedback. Say what you think. Express yourself.

This will have two critically important positive effects:

Feedback won’t be personal in your company. If the CEO constantly gives feedback, then everyone she interacts with will just get used to it. Nobody will think: “Gee, what did she really mean by that comment? Does she not like me?” Everybody will naturally focus on the issues, not an implicit random performance evaluation.

People will become comfortable discussing bad news. If people get comfortable talking about what each other are doing wrong, then it will be very easy to talk about what the company is doing wrong. High quality company cultures get their cue from data networking routing protocols: bad news travels fast and good news travels slowly. Low quality company cultures take on the personality of the Wicked Witch of the East in The Wiz: “Don’t nobody bring me no bad news.”

Making the CEO

Being CEO requires also a broad set of more advanced skills—I’ve written about many in this blog—but the key to reaching the advanced level and feeling like you were born to be CEO is mastering the unnatural.

If you are a founder CEO and you feel awkward or incompetent when doing some of these things and believe there is no way that you’ll be able to do it when your company is 100 or 1,000 people, welcome to the club. That’s exactly how I felt. So did every CEO that I’ve ever met. This is the process. This is how you get made.